7/2/1986 (33 years old) New York, New York, United States
This former child model underwent a striking transformation from freckle-faced cutie to curvaceous teen redhead to super-skinny blonde vixen whose personal woes overtook the bright promise of her early career successes. For while Lohan is a wonderful actress who possesses poise, charm and natural comic timing, it's her tempestuous life (which includes high-profile romances and substance-abuse issues) that keeps her in the spotlight. After appearing on a few daytime soaps, Lohan landed a dual role in Disney's big-screen remake of The Parent Trap in 1998. Her winning turn as a high-school rocker who switches bodies with her uptight mom in Disney's 2003 remake of Freaky Friday boosted her career, as did her amusing performance as a smart homeschooled student in 2004's Mean Girls. In addition to acting, Lohan continued to model, and recorded pop albums, often de rigueur for teen starlets of her generation. But popular as her projects were, her turbulent off-screen life (in direct contrast to her squeaky clean onscreen image) generated even more interest, including feuds with Hilary Duff and Paris Hilton, estrangement from her ex-con father, myriad romances, late-night carousing and her dramatic weight loss. In January 2007, after much speculation about her incessant partying, she checked herself into a swanky rehab. Her career stalled throughout the rest of the decade, as tabloid coverage far overshadowed professional success, though she did take on a film project, The Other Side, in 2009.